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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 4: 969 - 977

DOI: https://doi.org/10.6023/cjoc201909006

Efficient Synthesis of 1,4-Dihydropyridines and Polyhydroquinolines Catalyzed by Novel Schiff Base Zirconium Lewis Acid

  • Wang Jing ,
  • Jin Zhaohui ,
  • Ma Rong ,
  • Hao Yinjian ,
  • Wang Yijun ,
  • Li Ningbo ,
  • Xu Xinhua
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  • a Department of Preventive Medicine, School of Public Health, Shanxi Medical University, Taiyuan 030001;
    b Basic Medical College, Shanxi Medical University, Taiyuan 030001;
    c College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082

Received date: 2019-09-03

  Revised date: 2019-10-30

  Online published: 2020-05-06

Supported by

Project supported by the National Natural Science Foundation of China (No. 21802093), the Shanxi Province Science Foundation for Youths (No. 201701D221035) and the Scientific and Technologial Innovation Programs of Higher Education Institutions in Shanxi (No. 2019L0408).

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Abstract

A novel air-stable β-naphthol formaldehyde Schiff base zirconium perfluorooctanesulfonate Lewis acid catalyst was successfully synthesized by the reaction of β-naphthol formaldehyde Schiff base zirconium dichlorides with silver perfluorooctanesulfonate in the absence of light at room temperature. The results of catalytic assessment showed that this complex (5 mol%) could effectively catalyze the Hantzsch reaction of aldehydes, β-keto ester and ammonium acetate to obtain 1,4-dihydropyridine compounds at 80℃ under solvent-free conditions in good to excellent yields. Meanwhile, it could also effectively catalyze the reaction of aromatic aldehydes, cyclic β-diketone, β-keto ester and ammonium acetate to obtain 4-aryl polyhydroquinoline compounds. This catalyst could be reused 5 times, and the yields had no significant decrease. This procedure provides a simple and efficient way for the synthesis of 1,4-dihydropyridine and polyhydroquinoline compounds.

Key words： β-naphthol formaldehyde Schiff base; zirconium perfluorooctanesulfonate; Hantzsch reaction; 1,4-dihydro-pyridine; 4-aryl polyhydroquinoline

Cite this article

Wang Jing , Jin Zhaohui , Ma Rong , Hao Yinjian , Wang Yijun , Li Ningbo , Xu Xinhua . Efficient Synthesis of 1,4-Dihydropyridines and Polyhydroquinolines Catalyzed by Novel Schiff Base Zirconium Lewis Acid[J]. Chinese Journal of Organic Chemistry, 2020 , 40(4) : 969 -977 . DOI: 10.6023/cjoc201909006

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